JP2001521020A5 - - Google Patents
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- Publication number
- JP2001521020A5 JP2001521020A5 JP2000517936A JP2000517936A JP2001521020A5 JP 2001521020 A5 JP2001521020 A5 JP 2001521020A5 JP 2000517936 A JP2000517936 A JP 2000517936A JP 2000517936 A JP2000517936 A JP 2000517936A JP 2001521020 A5 JP2001521020 A5 JP 2001521020A5
- Authority
- JP
- Japan
- Prior art keywords
- acetic acid
- aminomethyl
- cyclopentyl
- methyl
- cyclobutyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 166
- 150000001875 compounds Chemical class 0.000 description 21
- CNCRBAYWBZGPBZ-HTQZYQBOSA-N (7R,8R)-7,8-dimethyl-2-azaspiro[4.4]nonan-3-one Chemical compound C1[C@@H](C)[C@H](C)CC11CC(=O)NC1 CNCRBAYWBZGPBZ-HTQZYQBOSA-N 0.000 description 10
- 239000003814 drug Substances 0.000 description 10
- 229910052739 hydrogen Inorganic materials 0.000 description 9
- 239000001257 hydrogen Substances 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 229910000564 Raney nickel Inorganic materials 0.000 description 4
- 239000012298 atmosphere Substances 0.000 description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 230000002194 synthesizing Effects 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- WVFKRUXAEOXLHW-HTQZYQBOSA-N 2-[(3R,4R)-3,4-dimethyl-1-(nitromethyl)cyclopentyl]acetic acid Chemical compound C[C@@H]1CC(CC(O)=O)(C[N+]([O-])=O)C[C@H]1C WVFKRUXAEOXLHW-HTQZYQBOSA-N 0.000 description 2
- 125000004432 carbon atoms Chemical group C* 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- OVCCKUOTVGFWJQ-UHFFFAOYSA-N ethyl 2-(3-benzylcyclobutylidene)acetate Chemical compound C1C(=CC(=O)OCC)CC1CC1=CC=CC=C1 OVCCKUOTVGFWJQ-UHFFFAOYSA-N 0.000 description 2
- XFBFXEQNMLQECT-NXEZZACHSA-N ethyl 2-[(3R,4R)-3,4-dimethyl-1-(nitromethyl)cyclopentyl]acetate Chemical compound CCOC(=O)CC1(C[N+]([O-])=O)C[C@@H](C)[C@H](C)C1 XFBFXEQNMLQECT-NXEZZACHSA-N 0.000 description 2
- QLHNVWKVWDIVIG-RKDXNWHRSA-N ethyl 2-[(3R,4R)-3,4-dimethylcyclopentylidene]acetate Chemical compound CCOC(=O)C=C1C[C@@H](C)[C@H](C)C1 QLHNVWKVWDIVIG-RKDXNWHRSA-N 0.000 description 2
- QLHNVWKVWDIVIG-DTORHVGOSA-N ethyl 2-[(3R,4S)-3,4-dimethylcyclopentylidene]acetate Chemical compound CCOC(=O)C=C1C[C@H](C)[C@H](C)C1 QLHNVWKVWDIVIG-DTORHVGOSA-N 0.000 description 2
- UDBYYPDEHJNWBE-UHFFFAOYSA-N ethyl 2-[1-(nitromethyl)cyclobutyl]acetate Chemical compound CCOC(=O)CC1(C[N+]([O-])=O)CCC1 UDBYYPDEHJNWBE-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- -1 hydroxy, hydroxymethyl Chemical group 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- OPAXRDNEIABTQI-VIFPVBQESA-N 2-[(1R)-1-(aminomethyl)-2,2-dimethylcyclobutyl]acetic acid Chemical compound CC1(C)CC[C@@]1(CN)CC(O)=O OPAXRDNEIABTQI-VIFPVBQESA-N 0.000 description 1
- DNHPJOLWCOXHOV-JTQLQIEISA-N 2-[(1R)-1-(aminomethyl)-2,2-dimethylcyclopentyl]acetic acid Chemical compound CC1(C)CCC[C@@]1(CN)CC(O)=O DNHPJOLWCOXHOV-JTQLQIEISA-N 0.000 description 1
- SIKUEILNNOXUAZ-LBPRGKRZSA-N 2-[(1R)-1-(aminomethyl)-3,3-diethylcyclopentyl]acetic acid Chemical compound CCC1(CC)CC[C@](CN)(CC(O)=O)C1 SIKUEILNNOXUAZ-LBPRGKRZSA-N 0.000 description 1
- QZBKCCCUSMQVTC-JTQLQIEISA-N 2-[(1R)-1-(aminomethyl)-3,3-dimethylcyclopentyl]acetic acid Chemical compound CC1(C)CC[C@](CN)(CC(O)=O)C1 QZBKCCCUSMQVTC-JTQLQIEISA-N 0.000 description 1
- OPAXRDNEIABTQI-SECBINFHSA-N 2-[(1S)-1-(aminomethyl)-2,2-dimethylcyclobutyl]acetic acid Chemical compound CC1(C)CC[C@]1(CN)CC(O)=O OPAXRDNEIABTQI-SECBINFHSA-N 0.000 description 1
- DNHPJOLWCOXHOV-SNVBAGLBSA-N 2-[(1S)-1-(aminomethyl)-2,2-dimethylcyclopentyl]acetic acid Chemical compound CC1(C)CCC[C@]1(CN)CC(O)=O DNHPJOLWCOXHOV-SNVBAGLBSA-N 0.000 description 1
- SIKUEILNNOXUAZ-GFCCVEGCSA-N 2-[(1S)-1-(aminomethyl)-3,3-diethylcyclopentyl]acetic acid Chemical compound CCC1(CC)CC[C@@](CN)(CC(O)=O)C1 SIKUEILNNOXUAZ-GFCCVEGCSA-N 0.000 description 1
- QZBKCCCUSMQVTC-SNVBAGLBSA-N 2-[(1S)-1-(aminomethyl)-3,3-dimethylcyclopentyl]acetic acid Chemical compound CC1(C)CC[C@@](CN)(CC(O)=O)C1 QZBKCCCUSMQVTC-SNVBAGLBSA-N 0.000 description 1
- VVJFYFLGWOCDQD-HTQZYQBOSA-N 2-[(2R,5R)-1-(aminomethyl)-2,5-dimethylcyclopentyl]acetic acid Chemical compound C[C@@H]1CC[C@@H](C)C1(CN)CC(O)=O VVJFYFLGWOCDQD-HTQZYQBOSA-N 0.000 description 1
- VVJFYFLGWOCDQD-YUMQZZPRSA-N 2-[(2S,5S)-1-(aminomethyl)-2,5-dimethylcyclopentyl]acetic acid Chemical compound C[C@H]1CC[C@H](C)C1(CN)CC(O)=O VVJFYFLGWOCDQD-YUMQZZPRSA-N 0.000 description 1
- FKLQZOOZJOUECB-VXGBXAGGSA-N 2-[(3R,4R)-1-(aminomethyl)-3,4-di(propan-2-yl)cyclopentyl]acetic acid Chemical compound CC(C)[C@H]1CC(CN)(CC(O)=O)C[C@@H]1C(C)C FKLQZOOZJOUECB-VXGBXAGGSA-N 0.000 description 1
- HBFZWKRCDVWGSA-WOJBJXKFSA-N 2-[(3R,4R)-1-(aminomethyl)-3,4-dibenzylcyclopentyl]acetic acid Chemical compound C([C@@H]1CC(C[C@H]1CC=1C=CC=CC=1)(CC(O)=O)CN)C1=CC=CC=C1 HBFZWKRCDVWGSA-WOJBJXKFSA-N 0.000 description 1
- KOPGUPUTANQKJY-NXEZZACHSA-N 2-[(3R,4R)-1-(aminomethyl)-3,4-diethylcyclopentyl]acetic acid Chemical compound CC[C@@H]1CC(CN)(CC(O)=O)C[C@H]1CC KOPGUPUTANQKJY-NXEZZACHSA-N 0.000 description 1
- IUVMAUQEZFTTFB-HTQZYQBOSA-N 2-[(3R,4R)-1-(aminomethyl)-3,4-dimethylcyclopentyl]acetic acid Chemical compound C[C@@H]1CC(CN)(CC(O)=O)C[C@H]1C IUVMAUQEZFTTFB-HTQZYQBOSA-N 0.000 description 1
- MJEPQHYIBKJJGY-SCLLHFNJSA-N 2-[(3R,4R)-1-(aminomethyl)-3,4-dimethylcyclopentyl]acetic acid;hydrochloride Chemical compound Cl.C[C@@H]1CC(CN)(CC(O)=O)C[C@H]1C MJEPQHYIBKJJGY-SCLLHFNJSA-N 0.000 description 1
- BHQDRZBQUNHTBG-ROUUACIJSA-N 2-[(3R,4R)-1-(aminomethyl)-3,4-diphenylcyclopentyl]acetic acid Chemical compound C1([C@H]2[C@@H](CC(C2)(CC(O)=O)CN)C=2C=CC=CC=2)=CC=CC=C1 BHQDRZBQUNHTBG-ROUUACIJSA-N 0.000 description 1
- DPSPUVHOQGLSSE-VXGBXAGGSA-N 2-[(3R,4R)-1-(aminomethyl)-3,4-ditert-butylcyclopentyl]acetic acid Chemical compound CC(C)(C)[C@@H]1CC(CN)(CC(O)=O)C[C@H]1C(C)(C)C DPSPUVHOQGLSSE-VXGBXAGGSA-N 0.000 description 1
- FKLQZOOZJOUECB-RYUDHWBXSA-N 2-[(3S,4S)-1-(aminomethyl)-3,4-di(propan-2-yl)cyclopentyl]acetic acid Chemical compound CC(C)[C@@H]1CC(CN)(CC(O)=O)C[C@H]1C(C)C FKLQZOOZJOUECB-RYUDHWBXSA-N 0.000 description 1
- HBFZWKRCDVWGSA-PMACEKPBSA-N 2-[(3S,4S)-1-(aminomethyl)-3,4-dibenzylcyclopentyl]acetic acid Chemical compound C([C@H]1CC(C[C@@H]1CC=1C=CC=CC=1)(CC(O)=O)CN)C1=CC=CC=C1 HBFZWKRCDVWGSA-PMACEKPBSA-N 0.000 description 1
- KOPGUPUTANQKJY-UWVGGRQHSA-N 2-[(3S,4S)-1-(aminomethyl)-3,4-diethylcyclopentyl]acetic acid Chemical compound CC[C@H]1CC(CN)(CC(O)=O)C[C@@H]1CC KOPGUPUTANQKJY-UWVGGRQHSA-N 0.000 description 1
- BHQDRZBQUNHTBG-QZTJIDSGSA-N 2-[(3S,4S)-1-(aminomethyl)-3,4-diphenylcyclopentyl]acetic acid Chemical compound C1([C@@H]2[C@H](CC(C2)(CC(O)=O)CN)C=2C=CC=CC=2)=CC=CC=C1 BHQDRZBQUNHTBG-QZTJIDSGSA-N 0.000 description 1
- DPSPUVHOQGLSSE-RYUDHWBXSA-N 2-[(3S,4S)-1-(aminomethyl)-3,4-ditert-butylcyclopentyl]acetic acid Chemical compound CC(C)(C)[C@H]1CC(CN)(CC(O)=O)C[C@@H]1C(C)(C)C DPSPUVHOQGLSSE-RYUDHWBXSA-N 0.000 description 1
- ZKPYVRKWQDIKJF-UHFFFAOYSA-N 2-[1-(aminomethyl)-2,2,3,3,4,4-hexamethylcyclobutyl]acetic acid Chemical compound CC1(C)C(C)(C)C(CN)(CC(O)=O)C1(C)C ZKPYVRKWQDIKJF-UHFFFAOYSA-N 0.000 description 1
- XRAYXEBZNYLCBY-UHFFFAOYSA-N 2-[1-(aminomethyl)-2,2,4,4-tetramethylcyclobutyl]acetic acid Chemical compound CC1(C)CC(C)(C)C1(CN)CC(O)=O XRAYXEBZNYLCBY-UHFFFAOYSA-N 0.000 description 1
- PSOWEDFUUXXEHX-UHFFFAOYSA-N 2-[1-(aminomethyl)-2,2,5,5-tetramethylcyclopentyl]acetic acid Chemical compound CC1(C)CCC(C)(C)C1(CN)CC(O)=O PSOWEDFUUXXEHX-UHFFFAOYSA-N 0.000 description 1
- SEPPWOWOFXDAAP-UHFFFAOYSA-N 2-[1-(aminomethyl)-3,3,4,4-tetraethylcyclopentyl]acetic acid Chemical compound CCC1(CC)CC(CN)(CC(O)=O)CC1(CC)CC SEPPWOWOFXDAAP-UHFFFAOYSA-N 0.000 description 1
- FLNCTXNXKXKYGH-UHFFFAOYSA-N 2-[1-(aminomethyl)-3,3,4,4-tetramethylcyclopentyl]acetic acid Chemical compound CC1(C)CC(CN)(CC(O)=O)CC1(C)C FLNCTXNXKXKYGH-UHFFFAOYSA-N 0.000 description 1
- UWYKQWDIAKQCEJ-UHFFFAOYSA-N 2-[1-(aminomethyl)-3,3-di(propan-2-yl)cyclobutyl]acetic acid Chemical compound CC(C)C1(C(C)C)CC(CN)(CC(O)=O)C1 UWYKQWDIAKQCEJ-UHFFFAOYSA-N 0.000 description 1
- SRLZVTNHASZZSM-UHFFFAOYSA-N 2-[1-(aminomethyl)-3,3-dibenzylcyclobutyl]acetic acid Chemical compound C1C(CN)(CC(O)=O)CC1(CC=1C=CC=CC=1)CC1=CC=CC=C1 SRLZVTNHASZZSM-UHFFFAOYSA-N 0.000 description 1
- BSRBEUFYGVVBLO-UHFFFAOYSA-N 2-[1-(aminomethyl)-3,3-diethylcyclobutyl]acetic acid Chemical compound CCC1(CC)CC(CN)(CC(O)=O)C1 BSRBEUFYGVVBLO-UHFFFAOYSA-N 0.000 description 1
- XEXRZUKGFDRWLE-UHFFFAOYSA-N 2-[1-(aminomethyl)-3,3-dimethylcyclobutyl]acetic acid Chemical compound CC1(C)CC(CN)(CC(O)=O)C1 XEXRZUKGFDRWLE-UHFFFAOYSA-N 0.000 description 1
- LJBMNGNDAMRUJV-UHFFFAOYSA-N 2-[1-(aminomethyl)-3,3-dimethylcyclopentyl]acetic acid;hydrochloride Chemical compound Cl.CC1(C)CCC(CN)(CC(O)=O)C1 LJBMNGNDAMRUJV-UHFFFAOYSA-N 0.000 description 1
- FUDBUFIPBPLPHY-UHFFFAOYSA-N 2-[1-(aminomethyl)-3,3-diphenylcyclobutyl]acetic acid Chemical compound C1C(CN)(CC(O)=O)CC1(C=1C=CC=CC=1)C1=CC=CC=C1 FUDBUFIPBPLPHY-UHFFFAOYSA-N 0.000 description 1
- CYOHDPOYWOPSRK-UHFFFAOYSA-N 2-[1-(aminomethyl)-3,3-ditert-butylcyclobutyl]acetic acid Chemical compound CC(C)(C)C1(C(C)(C)C)CC(CN)(CC(O)=O)C1 CYOHDPOYWOPSRK-UHFFFAOYSA-N 0.000 description 1
- UKPVCXAEJOKSRI-UHFFFAOYSA-N 2-[1-(aminomethyl)cyclobutyl]acetic acid;hydrochloride Chemical compound Cl.OC(=O)CC1(CN)CCC1 UKPVCXAEJOKSRI-UHFFFAOYSA-N 0.000 description 1
- RDJWDZURNKBDSS-UHFFFAOYSA-N 8,8-dimethyl-2-azaspiro[4.4]nonan-3-one Chemical compound C1C(C)(C)CCC11CC(=O)NC1 RDJWDZURNKBDSS-UHFFFAOYSA-N 0.000 description 1
- 206010002855 Anxiety Diseases 0.000 description 1
- 206010057666 Anxiety disease Diseases 0.000 description 1
- IUVMAUQEZFTTFB-YUMQZZPRSA-N Atagabalin Chemical compound C[C@H]1CC(CN)(CC(O)=O)C[C@@H]1C IUVMAUQEZFTTFB-YUMQZZPRSA-N 0.000 description 1
- 206010010904 Convulsion Diseases 0.000 description 1
- 206010015037 Epilepsy Diseases 0.000 description 1
- 208000008665 Gastrointestinal Disease Diseases 0.000 description 1
- 208000006083 Hypokinesia Diseases 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 208000002551 Irritable Bowel Syndrome Diseases 0.000 description 1
- 206010053643 Neurodegenerative disease Diseases 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- 206010039911 Seizure Diseases 0.000 description 1
- 206010042772 Syncope Diseases 0.000 description 1
- 230000036506 anxiety Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000003818 flash chromatography Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- 201000002146 gastrointestinal system disease Diseases 0.000 description 1
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 description 1
- 230000003483 hypokinetic Effects 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- IMNFDUFMRHMDMM-UHFFFAOYSA-N n-heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 1
- 230000002981 neuropathic Effects 0.000 description 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US6364497P | 1997-10-27 | 1997-10-27 | |
| US60/063,644 | 1997-10-27 | ||
| US9768598P | 1998-08-24 | 1998-08-24 | |
| US60/097,685 | 1998-08-24 | ||
| PCT/US1998/019876 WO1999021824A1 (en) | 1997-10-27 | 1998-09-23 | Cyclic amino acids and derivatives thereof useful as pharmaceutical agents |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2005319009A Division JP4263717B2 (ja) | 1997-10-27 | 2005-11-02 | 医薬として有用な環状アミノ酸およびその誘導体 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2001521020A JP2001521020A (ja) | 2001-11-06 |
| JP2001521020A5 true JP2001521020A5 (pt) | 2006-01-05 |
| JP3756761B2 JP3756761B2 (ja) | 2006-03-15 |
Family
ID=26743626
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000517936A Expired - Fee Related JP3756761B2 (ja) | 1997-10-27 | 1998-09-23 | 医薬として有用な環状アミノ酸およびその誘導体 |
| JP2005319009A Expired - Fee Related JP4263717B2 (ja) | 1997-10-27 | 2005-11-02 | 医薬として有用な環状アミノ酸およびその誘導体 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2005319009A Expired - Fee Related JP4263717B2 (ja) | 1997-10-27 | 2005-11-02 | 医薬として有用な環状アミノ酸およびその誘導体 |
Country Status (31)
| Country | Link |
|---|---|
| US (3) | US6635673B1 (pt) |
| EP (1) | EP1032555B1 (pt) |
| JP (2) | JP3756761B2 (pt) |
| KR (1) | KR100589066B1 (pt) |
| CN (2) | CN1303059C (pt) |
| AR (1) | AR013726A1 (pt) |
| AT (1) | ATE323067T1 (pt) |
| AU (1) | AU755800B2 (pt) |
| BR (1) | BR9813284B1 (pt) |
| CA (1) | CA2303244C (pt) |
| CO (1) | CO5280097A1 (pt) |
| CU (1) | CU23048A3 (pt) |
| CY (1) | CY1105062T1 (pt) |
| DE (1) | DE69834204T2 (pt) |
| DK (1) | DK1032555T3 (pt) |
| ES (1) | ES2260850T3 (pt) |
| GE (1) | GEP20094817B (pt) |
| HK (2) | HK1030768A1 (pt) |
| HU (1) | HUP0004310A3 (pt) |
| IL (1) | IL134732A (pt) |
| IS (1) | IS2489B (pt) |
| NO (1) | NO327671B1 (pt) |
| NZ (1) | NZ503651A (pt) |
| PE (1) | PE122799A1 (pt) |
| PL (2) | PL199794B1 (pt) |
| PT (1) | PT1032555E (pt) |
| SI (1) | SI1032555T1 (pt) |
| TR (1) | TR200001170T2 (pt) |
| UY (1) | UY25223A1 (pt) |
| WO (1) | WO1999021824A1 (pt) |
| ZA (1) | ZA989740B (pt) |
Families Citing this family (70)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU225502B1 (en) * | 1998-12-29 | 2007-01-29 | Richter Gedeon Vegyeszet | Process for producing 1-(amino-metyl)-cyclohexene-acetic-acid and intermediates |
| PT1180094E (pt) * | 1999-05-26 | 2004-10-29 | Warner Lambert Co | Aminoacidos policiclicos fundidos como agentes farmaceuticos |
| OA11962A (en) * | 1999-06-10 | 2006-04-17 | Warner Lambert Co | Mono-and disubstituted 3-propyl gamma-aminobutyricacids. |
| US7164034B2 (en) | 1999-06-10 | 2007-01-16 | Pfizer Inc. | Alpha2delta ligands for fibromyalgia and other disorders |
| EP1840117A1 (en) * | 1999-06-10 | 2007-10-03 | Warner-Lambert Company LLC | Mono- and disubstituted 3-propyl gamma-aminobutyric acids |
| US6642398B2 (en) | 1999-06-10 | 2003-11-04 | Warner-Lambert Company | Mono-and disubstituted 3-propyl gamma-aminobutyric acids |
| HN2000000224A (es) | 1999-10-20 | 2001-04-11 | Warner Lambert Co | Aminoacidos biciclicos como agentes farmaceuticos |
| HUP0203812A3 (en) * | 1999-12-08 | 2004-12-28 | Warner Lambert Co | Method for the stereoselective synthesis of cyclic amino acids |
| US6864390B2 (en) | 1999-12-08 | 2005-03-08 | Warner-Lambert Company | Method for the stereoselective synthesis of cyclic amino acids |
| GB2362646A (en) * | 2000-05-26 | 2001-11-28 | Warner Lambert Co | Cyclic amino acid derivatives useful as pharmaceutical agents |
| MXPA02010668A (es) | 2000-06-26 | 2003-03-10 | Warner Lambert Co | Analogos de gabapentina para alteraciones del sueno. |
| GB2364049A (en) * | 2000-06-28 | 2002-01-16 | Warner Lambert Co | Cyclic ketones and their use in the synthesis of amino acids |
| AU2002230398A1 (en) | 2000-10-06 | 2002-04-29 | Xenoport, Inc. | Bile-acid conjugates for providing sustained systemic concentrations of drugs |
| AU2002211863A1 (en) | 2000-10-06 | 2002-04-15 | Xenoport, Inc. | Bile-acid derived compounds for providing sustained systemic concentrations of drugs after oral administration |
| EP1226820A1 (en) * | 2001-01-26 | 2002-07-31 | Warner-Lambert Company | Use of bicyclic amino acids for preventing and treating visceral pain and gastrointestinal disorders |
| EA006396B1 (ru) * | 2001-04-19 | 2005-12-29 | УОРНЕР-ЛАМБЕРТ КОМПАНИ Эл Эл Си | Конденсированные бициклические аминокислоты |
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